They Made Him Wear Dresses and Pink Clothes

DEAR ABBY: My brother and sister-in-law have been dressing my nephew, “Charlie,” in dresses and pink clothes. They say these are what the boy has chosen.

It would be one thing if Charlie were old enough to understand and still insisted he felt more comfortable in girls’ clothing. But at his age I feel what they’re doing will only confuse him. My sister-in-law knows this upsets my mother and yet it’s like she’s taunting her with texts and pictures of Charlie in pink and/or dresses.

Should we be worried about this or should it be none of our business? Are we overreacting? Would it be best to approach my brother to tell him our concerns? — TOO YOUNG TO UNDERSTAND

Maybe they should wait until he’s old enough to understand, what’s the worst that can happen?

Under the Hood by DovSherman

Under the Hood by DovSherman

Artwork by DovSherman on DeviantArt and posted under Crossdress, Curlers, Femdom, Humiliation, Salon and Sissy.

Salon Sissy Cry Baby

An unidentified Australian beauty parlor now charges an extra $10 for children who break down in tears when they’re getting a new hairdo. Now is that really what you want? That money can go towards a tip so the girls give you the best chair next time.

Just keep saying to yourself: big boys don’t cry, big boys don’t cry, big boys don’t cry.

Big Boys Don’t Cry

Big Boys Don’t Cry

The Sissy Walk of Shame

This is one of four illustrations that Rocket Dave made me for my caught in panties story a while back. I like this one the best because I think he really captured the sissy walk of shame into the beauty salon. Note: not every sissy has such great legs.

Click here to see larger

The Sissy Walk of Shame

The Sissy Walk of Shame

Sissy Audio-Special Requests

I am recording again and will be adding to my Podcast very soon. If you have suggestions or special requests leave a comment below.

Sissy stories will be considered but must be less than 1000 words. A good example is Saragirl’s Sissy Confession (see my story page or Podcast). Do not send me anything without discussing it first, there are only 24 little hours in a day.

Topics can include forced feminization, sissy humiliation, transvestite bondage, sissy maids, or all of the above. But absolutely no more cheerleader fantasies, too many torn ligaments.

Cheers

Cheers

A Portrait of a Crossdressing Caption Artist-The Sublime and the Ridiculous

Me: So how did you get into making crossdressing captions Arthur?

Art: Good question. I retired several years ago, and nothing I did was really satisfying. Sure, I have motorcycles, race cars and other hobbies, but I felt stressed out most of the time. One day I was coming home from a long ride, passed a little beauty salon in the middle of nowhere, and for some reason started thinking about forced feminization. That night I made my first caption. After that it became what I feel is a very creative outlet and an excellent stress reliever. What do you think?

Me: Well to be honest I think it’s a bit silly, if not completely ridiculous. What are your other hobbies?

Art: I take pictures of old cameras in the woods. Sometimes I’ll ride a hundred miles to find the right place and set everything up, then take thousands of photos. They are my interpretation of the sublime aspects of reality.

Me: Interesting. So what, in your opinion, is reality Arthur?

Art: It’s a bitch Teresa.

Me: Agreed.

The Sublime and the Ridiculous

The Sublime and the Ridiculous

They Made Him a Prissy Sissy Schoolie Slut

I wrote this story last spring, and it’s one of the most visited posts after Crossdressing With Aunt Christy-A True Story. There is a possibility that I will record this for my Podcast. Now let’s take a trip to Sissy School:

(Correction-it seems that I originally wrote this in 2013 when I was selling sissy dresses.)

The forced feminization school girl fantasy is an all time favorite among sissies. Somehow the girls at school discover that you like to dress up when you’re home alone.

Do they keep this a secret? Do they simply ignore the fact that you like to wear panties, lingerie and dresses at home, then pretend to be one of the guys at school?

No, not a chance.

Pretty girls have certain priorities while they’re in school, and one of the most important is power. Now all pretty girls have quite a bit of power just by being pretty, and knowing that, most of the boys are infatuated with them.

They also know that a little smile or touch at the right time can turn most boys into a quivering mess of nerves and fear.

What happens when they realize that they have you by the balls, and can make you do almost anything they want? They can make things very hard for you very fast…

READ MORE HERE

They Made Him A Prissy Sissy Schoolie Slut

They Made Him A Prissy Sissy Schoolie Slut

Feminized by Mom and Her Friend

Getting caught in the panty drawer and feminized as punishment is a favorite fantasy for all crossdressers, transvestites and sissies. Getting caught and feminized by your Mother, and getting caught and feminized by your Mother’s friend are two very different things though.

These are actually two separate stories about the same boy. In the first one, Mom calls her friend to see if she can help. Her friend has a lot of experience with boys that dress like girls, and tries a crossdressing intervention to see if he is really the sissy he seems to be. She has limited success but he has a ball. What now?

Mom decides to take the matter into her own hands. She encourages her son to dress like a girl until the thrill is gone. But that doesn’t happen right away. It takes him a tremendous amount of practice and hundreds of pairs of panties to come to his own conclusion about the whole thing.

Both are audio stories as well as written stories, listen to the previews or read the whole thing. These two recordings and 14 others are free with a one time video signup, you’ll see the link. Enjoy!

Feminized by Mom’s Friend

Feminized by Mom

Feminized by Mom and Her Friend

Feminized by Mom and Her Friend

He dresses up as a girl and has sex with men

Teresa asked me to confess my hottest fantasy, the hottest fantasy of my dirty, sissy mind. I have several, of course, I have quite the active mind, some are kind of vanilla (relatively so, I mean, S/M is kind of vanilla, right?)

Strap on sex…that’s a hot fantasy…but the hottest? Bride, French Maid. Hot, yes, but hottest?

Because I’m thinking not just “hottest” but naughty, even taboo. And I’m not just thinking fantasy, but something that I’d toe the line about turning into reality…almost.

What is my hottest fantasy, then? I want to submit to a man. Wait, that’s not so hot, is it?

Maybe not, but there’s a twist, a small, subtle twist that, if it happened, would drive me wild day after day after day. The twist? I want to submit to a man I know.

Again, not that hot…but wait, there’s more…

READ MORE HERE

Sissy Confessions

Sissy Confessions

The Holiday Sissy

When you wish upon a star, makes no difference who you are. Anything your heart desires will come to you. If your heart is in your dream, no request is too extreme. When you wish upon a star, as dreamers do.

Happy holidays and may all your dreams come true.

Dream a little dream

Dream a little dream

Sissy Maid Tips

The most important tip is to stay out of her panty drawer. That’s how you got in trouble in the first place!

Trouble, trouble, trouble

Trouble, trouble, trouble